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Undecanoic Acid

PubChem CID
8180
Structure
Undecanoic Acid_small.png
Undecanoic Acid_3D_Structure.png
Undecanoic Acid__Crystal_Structure.png
Molecular Formula
Synonyms
  • UNDECANOIC ACID
  • 112-37-8
  • Hendecanoic acid
  • Undecylic acid
  • undecanoate
Molecular Weight
186.29 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2024-12-27
Description
Undecanoic acid is a white crystalline solid. Insoluble in water. Specific gravity 0.85. Hence floats on water.
Undecanoic acid is a straight-chain, eleven-carbon saturated medium-chain fatty acid found in body fluids; the most fungitoxic of the C7:0 - C18:0 fatty acid series. It has a role as a human metabolite and an antifungal agent. It is a straight-chain saturated fatty acid and a medium-chain fatty acid. It is a conjugate acid of an undecanoate. It derives from a hydride of an undecane.
Undecanoic acid has been reported in Leea guineensis, Streptomyces, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Undecanoic Acid.png

1.2 3D Conformer

1.3 Crystal Structures

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CCDC Number
Associated Article
Crystal Structure Data
Crystal Structure Depiction
Crystal Structure Depiction

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

undecanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C11H22O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2-10H2,1H3,(H,12,13)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

ZDPHROOEEOARMN-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCCCCCCCCCC(=O)O
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)

2.2 Molecular Formula

C11H22O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

112-37-8

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DrugBank ID

2.3.7 DSSTox Substance ID

2.3.8 FEMA Number

2.3.9 HMDB ID

2.3.10 JECFA Number

108

2.3.11 KEGG ID

2.3.12 Lipid Maps ID (LM_ID)

2.3.13 Metabolomics Workbench ID

2.3.14 NCI Thesaurus Code

2.3.15 Nikkaji Number

2.3.16 NSC Number

2.3.17 Pharos Ligand ID

2.3.18 Wikidata

2.3.19 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

undecanoic acid

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
186.29 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
3.7
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
9
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
186.161979940 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
186.161979940 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
37.3Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
13
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
121
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Undecanoic acid is a white crystalline solid. Insoluble in water. Specific gravity 0.85. Hence floats on water.
Other Solid
White solid; mp= 28.5 deg C; [CHRIS] Colorless solidified mass or fragments; mp = 28-31 deg C; [Sigma-Aldrich MSDS]
Solid
colourless crystals/ faint fatty, aldehydic odour

3.2.2 Boiling Point

442.2 °F at 160 mmHg (USCG, 1999)
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.

3.2.3 Melting Point

83.3 °F (USCG, 1999)
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.
28.6 °C

3.2.4 Flash Point

greater than 230 °F (USCG, 1999)
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.

3.2.5 Solubility

0.0522 mg/mL
Insoluble in water; very soluble in alcohol, chloroform, acetone

3.2.6 Density

0.891 (USCG, 1999) - Less dense than water; will float
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.
0.9948 (20°/20°)

3.2.7 LogP

4.42
SANGSTER (1993)

3.2.8 Refractive Index

1.4355 (30°)

3.2.9 Collision Cross Section

148.87 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

3.2.10 Kovats Retention Index

Standard non-polar
1460, 1488, 1493, 1469, 1445, 1474
Semi-standard non-polar
1466.8, 1490, 1468, 1490, 1465, 1465, 1490, 1482, 249.52, 248
Standard polar
2398, 2421, 2419, 2365, 2407, 2405, 2417, 2400, 2369, 2379, 2373, 2400, 2407, 2413, 2400, 2371, 2359, 2400, 2394, 2394, 2400, 2417, 2419, 2401, 2402.6, 2400

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Other Classes -> Organic Acids

3.4.1 Cosmetics

Cosmetic ingredients (Undecanoic Acid) -> CIR (Cosmetic Ingredient Review)
Emulsifying; Cleansing; Antiseborrhoeic
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

3.4.2 Food Additives

FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

3.4.3 Fragrances

Fragrance Ingredient (Undecanoic acid) -> IFRA transparency List

3.4.4 Lipids

Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Straight chain fatty acids [FA0101]

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 5
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Spectra ID
Instrument Type
Varian
Frequency
600 MHz
Solvent
Water
pH
7.01
Shifts [ppm]:Intensity
0.85:61.15, 1.27:100.00, 1.53:11.69, 2.14:15.58, 0.84:24.98, 2.17:13.93, 1.51:7.93, 2.15:26.97, 1.54:7.16, 0.86:21.06
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Spectra ID
Instrument Type
JEOL
Frequency
90 MHz
Solvent
CDCl3
Shifts [ppm]:Intensity
1.48:33.00, 0.92:67.00, 1.69:31.00, 2.42:47.00, 1.70:32.00, 2.43:45.00, 1.71:32.00, 1.49:32.00, 1.59:37.00, 2.27:101.00, 1.43:47.00, 1.55:39.00, 1.52:30.00, 1.40:58.00, 1.56:39.00, 1.57:38.00, 1.68:31.00, 1.61:44.00, 0.94:74.00, 1.27:1000.00, 1.55:38.00, 1.52:32.00, 1.63:49.00, 1.63:48.00, 1.67:33.00, 1.44:45.00, 2.35:126.00, 0.88:232.00, 1.54:37.00, 1.71:33.00, 1.47:34.00, 0.81:53.00
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4.1.2 13C NMR Spectra

1 of 4
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Spectra ID
Instrument Type
Varian
Frequency
25.16 MHz
Solvent
CDCl3
Shifts [ppm]:Intensity
29.18:798.00, 29.37:990.00, 34.25:640.00, 29.41:1000.00, 32.00:704.00, 29.66:931.00, 14.14:596.00, 29.54:931.00, 180.76:571.00, 22.77:828.00, 24.77:739.00
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Spectra ID
Instrument Type
Bruker
Solvent
CDCl3
Shifts [ppm]:Intensity
25.10:94.50, 29.86:76.54, 34.52:90.18, 180.81:33.88, 29.73:81.54, 32.32:84.40, 23.11:66.08, 29.67:103.39, 29.98:96.16, 29.49:97.12, 14.53:59.06
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4.2 2D NMR Spectra

4.2.1 1H-13C NMR Spectra

2D NMR Spectra Type
1H-13C HSQC
Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
CDCl3
pH
7.00
Shifts [ppm] (F2:F1):Intensity
1.64:24.70:0.23, 2.35:34.12:0.28, 0.88:14.20:0.06, 1.33:29.06:0.24, 1.29:22.75:0.16, 1.25:31.89:0.24, 1.26:29.38:1.00
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4.3 Mass Spectrometry

4.3.1 GC-MS

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Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

60.0 99.99

73.0 90.02

41.0 76.89

43.0 69.96

55.0 48.08

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Notes
instrument=HITACHI M-80B
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Spectra ID
Instrument Type
GC-MS
Top 5 Peaks

117.0 1

129.0 0.40

243.0 0.40

132.0 0.31

131.0 0.22

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4.3.2 MS-MS

1 of 7
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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

185.1552 100

186.1581 8.51

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2 of 7
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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

185.1545 100

186.1582 7.51

167.143 2.50

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4.3.3 LC-MS

1 of 12
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Accession ID
Authors
Plant Biology, The Noble Foundation, Ardmore, OK, US/Dennis Fine, Daniel Wherritt, and Lloyd Sumner
Instrument
Bruker impact HD
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
10 eV
Column Name
Waters Acquity BEH C18 1.7um x 2.1 x 150 mm
Retention Time
1313.4 sec
Precursor m/z
185.1552
Precursor Adduct
[M-H]-
Top 5 Peaks

185.1552 999

186.1581 85

187.1605 6

185.5854 5

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License
CC BY-NC-SA
2 of 12
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Accession ID
Authors
Plant Biology, The Noble Foundation, Ardmore, OK, US/Dennis Fine, Daniel Wherritt, and Lloyd Sumner
Instrument
Bruker impact HD
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
20 eV
Column Name
Waters Acquity BEH C18 1.7um x 2.1 x 150 mm
Retention Time
1313.4 sec
Precursor m/z
185.1545
Precursor Adduct
[M-H]-
Top 5 Peaks

185.1545 999

186.1582 75

167.143 25

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License
CC BY-NC-SA

4.3.4 Other MS

1 of 4
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Authors
SODA AROMATIC CO., LTD.
Instrument
HITACHI M-80B
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

60 999

73 900

41 769

43 700

55 481

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License
CC BY-NC-SA
2 of 4
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MS Category
Experimental
MS Type
Other
MS Level
MS2
Instrument Type
ESI-TOF
Ionization Mode
negative
Top 5 Peaks

213.1871 100

214.1901 13.91

449.3617 5.51

313.1112 4.60

281.1739 2.90

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4.4 IR Spectra

4.4.1 FTIR Spectra

1 of 2
Technique
CAPILLARY CELL: MELT
Source of Sample
Lachat Chemicals, Inc., Chicago Heights, Illinois
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
Melt (Liquid)
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Alfa Aesar, Thermo Fisher Scientific
Catalog Number
A11244
Lot Number
W16B021
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4.2 ATR-IR Spectra

1 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
TCI Chemicals India Pvt. Ltd.
Catalog Number
A11244
Lot Number
W16B021
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Sample
Aldrich
Catalog Number
171476
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4.3 Vapor Phase IR Spectra

1 of 2
Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Technique
Vapor Phase
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Aldrich
Catalog Number
171476
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.5 Raman Spectra

1 of 2
Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Alfa Aesar, Thermo Fisher Scientific
Catalog Number
A11244
Lot Number
W16B021
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Catalog Number
171476
Copyright
Copyright © 2017-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2017-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Food Additive Classes

Flavoring Agents
JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT;

7.2 FEMA Flavor Profile

Oil

7.3 FDA Substances Added to Food

Used for (Technical Effect)
FLAVORING AGENT OR ADJUVANT
FEMA Number
3245
GRAS Number
4
JECFA Flavor Number
108

7.4 Associated Foods

7.5 Evaluations of the Joint FAO / WHO Expert Committee on Food Additives - JECFA

Chemical Name
UNDECANOIC ACID
Evaluation Year
1997
ADI
No safety concern at current levels of intake when used as a flavouring agent
Tox Monograph

8 Pharmacology and Biochemistry

8.1 Human Metabolite Information

8.1.1 Cellular Locations

  • Extracellular
  • Membrane

9 Use and Manufacturing

9.1 Uses

Cosmetic Ingredient Review Link
CIR ingredient: Undecanoic Acid
EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
Sources/Uses
Used as flavoring agent or adjuvant; [FDA]

9.1.1 Use Classification

Food additives -> Flavoring Agents
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Cosmetics -> Emulsifying; Cleansing; Antiseborrhoeic
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

9.1.2 Industry Uses

  • Agricultural chemicals (non-pesticidal)
  • Lubricants and lubricant additives

9.1.3 Consumer Uses

Agricultural chemicals (non-pesticidal)

9.2 U.S. Production

Aggregated Product Volume

2019: <1,000,000 lb

2018: <1,000,000 lb

2017: <1,000,000 lb

2016: <1,000,000 lb

9.3 General Manufacturing Information

Industry Processing Sectors
  • Food, beverage, and tobacco product manufacturing
  • All Other Basic Organic Chemical Manufacturing
  • Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing
EPA TSCA Commercial Activity Status
Undecanoic acid: ACTIVE

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Note
Pictograms displayed are for 99.1% (209 of 211) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 0.9% (2 of 211) of reports.
Pictogram(s)
Corrosive
Irritant
Signal
Danger
GHS Hazard Statements

H314 (20.9%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

H315 (78.2%): Causes skin irritation [Warning Skin corrosion/irritation]

H318 (20.9%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H319 (66.8%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (65.4%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P260, P261, P264, P264+P265, P271, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P332+P317, P337+P317, P362+P364, P363, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 211 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 2 of 211 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 10 notifications provided by 209 of 211 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Skin Corr. 1C (20.9%)

Skin Irrit. 2 (78.2%)

Eye Dam. 1 (20.9%)

Eye Irrit. 2 (66.8%)

STOT SE 3 (65.4%)

10.1.3 Health Hazards

May be harmful by inhalation, ingestion or skin absorption. Material is irritating to mucous membrane and upper respiratory tract. Causes eye and skin irritation. (USCG, 1999)
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.

10.1.4 Fire Hazards

Special Hazards of Combustion Products: Dust explosion is possible. (USCG, 1999)
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.

10.1.5 Hazards Summary

A mild skin irritant; Causes convulsions in intravenous lethal-dose studies of mice; [RTECS] Causes severe skin irritation and serious eye injury; Brief contact can causes second- and third-degree skin burns; Vapors, dust, or mist causes severe eye and throat irritation and may cause injury to the eye and lung; [CHRIS] Safe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; [Sigma-Aldrich MSDS]

10.2 First Aid Measures

10.2.1 First Aid

INHALATION: Call for medical aid. Remove the victim to fresh air. If not breathing give artificial respiration. If breathing is difficult give oxygen.

EYES OR SKIN: Flush with copious amounts of water for at least 15 minutes. Insure adequate flushing of the eyes by separating the eyelids with the fingers. (USCG, 1999)

U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.

10.3 Fire Fighting

Fire Extinguishing Agents Not to Be Used: Water may not be effective.

Fire Extinguishing Agents: Carbon dioxide, dry chemical, alcohol foam, water spray. (USCG, 1999)

U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.

10.4 Handling and Storage

10.4.1 Nonfire Spill Response

Neutralizing Agents for Acids and Caustics: Sodium bicarbonate solution (USCG, 1999)
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.

10.5 Stability and Reactivity

10.5.1 Air and Water Reactions

Dust explosion is possible. (USCG, 1999). Insoluble in water.
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.

10.5.2 Reactive Group

Acids, Carboxylic

10.5.3 Reactivity Profile

A weak carboxylic acid. Neutralizes bases with the evolution of substantial amounts of heat to produce water plus a salt. Reacts with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Can generate flammable and/or toxic gases and heat by reaction with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Reacts in with aqueous solutions of nitrites and thiosulfates (to give H2S and SO3) and dithionites (to give SO2) and heat. Reaction with solutions of carbonates and bicarbonates generate a harmless gas (carbon dioxide) but still heat. Can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. May initiate polymerization reactions. May serve as a catalyst.

10.6 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Undecanoic acid
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Undecanoic acid: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

10.7 Other Safety Information

Chemical Assessment
Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment

11 Toxicity

11.1 Toxicological Information

11.1.1 Adverse Effects

Dermatotoxin - Skin burns.

Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.

11.1.2 Acute Effects

12 Associated Disorders and Diseases

Disease
Colorectal cancer
References

PubMed: 7482520, 22148915, 19006102, 23940645, 24424155, 20156336, 19678709, 25105552, 21773981, 25037050, 27015276, 27107423, 27275383, 28587349

Silke Matysik, Caroline Ivanne Le Roy, Gerhard Liebisch, Sandrine Paule Claus. Metabolomics of fecal samples: A practical consideration. Trends in Food Science & Technology. Vol. 57, Part B, Nov. 2016, p.244-255: http://www.sciencedirect.com/science/article/pii/S0924224416301984

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Thieme References

13.5 Wiley References

13.6 Chemical Co-Occurrences in Literature

13.7 Chemical-Gene Co-Occurrences in Literature

13.8 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Protein Bound 3D Structures

15.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Conformer

15.2 Chemical-Target Interactions

16 Biological Test Results

16.1 BioAssay Results

17 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
A metabolome atlas of the aging mouse brain. Nat Commun. 2021 Oct 15;12(1):6021. DOI:10.1038/s41467-021-26310-y. PMID:34654818; PMCID:PMC8519999.
The Metabolome Atlas of the Aging Mouse Brain: https://mouse.atlas.metabolomics.us

18 Classification

18.1 MeSH Tree

18.2 NCI Thesaurus Tree

18.3 ChEBI Ontology

18.4 LIPID MAPS Classification

18.5 KEGG: Lipid

18.6 ChemIDplus

18.7 CAMEO Chemicals

18.8 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

18.9 ChEMBL Target Tree

18.10 UN GHS Classification

18.11 EPA CPDat Classification

18.12 NORMAN Suspect List Exchange Classification

18.13 CCSBase Classification

18.14 EPA DSSTox Classification

18.15 EPA TSCA and CDR Classification

18.16 LOTUS Tree

18.17 EPA Substance Registry Services Tree

18.18 MolGenie Organic Chemistry Ontology

19 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAMEO Chemicals
    LICENSE
    CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data.
    https://cameochemicals.noaa.gov/help/reference/terms_and_conditions.htm?d_f=false
    CAMEO Chemical Reactivity Classification
    https://cameochemicals.noaa.gov/browse/react
  3. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  4. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  5. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  6. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  7. EPA Chemical Data Reporting (CDR)
    LICENSE
    The U.S. Government retains a nonexclusive, royalty-free license to publish or reproduce these documents, or allow others to do so, for U.S. Government purposes. These documents may be freely distributed and used for non-commercial, scientific and educational purposes.
    https://www.epa.gov/web-policies-and-procedures/epa-disclaimers#copyright
  8. EPA Chemicals under the TSCA
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  9. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  10. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  11. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  12. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  13. International Fragrance Association (IFRA)
    LICENSE
    (c) The International Fragrance Association, 2007-2021. All rights reserved.
    https://ifrafragrance.org/links/copyright
  14. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  15. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  16. Joint FAO/WHO Expert Committee on Food Additives (JECFA)
    LICENSE
    Permission from WHO is not required for the use of WHO materials issued under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Intergovernmental Organization (CC BY-NC-SA 3.0 IGO) licence.
    https://www.who.int/about/policies/publishing/copyright
  17. ChEBI
  18. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  19. Yeast Metabolome Database (YMDB)
    LICENSE
    YMDB is offered to the public as a freely available resource.
    http://www.ymdb.ca/downloads
  20. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  21. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  22. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  23. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  24. IUPHAR/BPS Guide to PHARMACOLOGY
    LICENSE
    The Guide to PHARMACOLOGY database is licensed under the Open Data Commons Open Database License (ODbL) https://opendatacommons.org/licenses/odbl/. Its contents are licensed under a Creative Commons Attribution-ShareAlike 4.0 International License (http://creativecommons.org/licenses/by-sa/4.0/)
    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  25. Therapeutic Target Database (TTD)
  26. Cosmetic Ingredient Review (CIR)
  27. EPA Chemical and Products Database (CPDat)
  28. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  29. Crystallography Open Database (COD)
    LICENSE
    All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data.
    https://creativecommons.org/publicdomain/zero/1.0/
  30. EU Food Improvement Agents
  31. FDA Substances Added to Food
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  32. Flavor and Extract Manufacturers Association (FEMA)
  33. FooDB
    LICENSE
    FooDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (FooDB) and the original publication.
    https://foodb.ca/about
  34. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  35. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  36. SpectraBase
  37. Japan Chemical Substance Dictionary (Nikkaji)
  38. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  39. KNApSAcK Species-Metabolite Database
  40. Natural Product Activity and Species Source (NPASS)
  41. West Coast Metabolomics Center-UC Davis
    FA 11:0;
  42. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  43. MassBank Europe
  44. Metabolomics Workbench
  45. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  46. Pharos
    LICENSE
    Data accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.
    https://pharos.nih.gov/about
  47. Protein Data Bank in Europe (PDBe)
  48. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  49. Springer Nature
  50. SpringerMaterials
  51. The Cambridge Structural Database
  52. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  53. Wikidata
  54. Wikipedia
  55. Wiley
  56. PubChem
  57. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  58. GHS Classification (UNECE)
  59. EPA Substance Registry Services
  60. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  61. PATENTSCOPE (WIPO)
  62. NCBI
CONTENTS